New azo dyestuffs



i and m mean aromatic nuclei which may be Patentedv June 16, 1931 Iume'rnn STATES- PATIENT? otrF-icE.

:rosnn HALLER, or" WIESDOBF-ON-THE-RHINE, ornamiinm nssrenon' T0 GENERALI ANILINE worms, 1110., OF NEW YORK, N. Y., A. CORPORATION or DELAWARE.

NEW .AZO DYESTUFIES No Drawing. Application filed April 2, 1928,,Seria1nofacasis, and in. Germany April 16, 1927.

The present invention relates to new azodyestuffs.

I have found that new azodyestufl's of the probable general formula:

1 CO.NH.I

the 0-position to the -N=Ngroupand which may be otherwise substituted bysubstituents not causing solubility 1n water, such as sulfoandcarboxylic acid groups, and R- substituted by substituents not causingsolubility in water, are obtainable by reacting with a suitable arylamidof 2.8-hydroxynaphthoic acid upon a suitable diazotizedaminoazo-compound obtained by coupling an ohydroxy-diazo compound withan aromatic amine which is capable of further diazotization.

Obviously these dyestuffs may be either in substanceor on the fiber.

The products thus obtainable form dark powders, insoluble in water,sparingly soluble in the usual organic solvents, soluble .in strongsulfuric acid with violet-blue to blue colorations, dyeing the fiberstrong violetblack to greenish-black shades, the fastnessproperties ofwhich are improved by aftertreatment with suitable metal salts such ascopperor chromium salts.

Thefollowing examples illustrate myin rvention, without limiting itthereto:

Example 1.2.7 parts by weight of the dyestuff obtainable by couplingdiazotize'd o-aminophenol with amino-hydroquinonedi- NO on methyletherare dissolved in 200 parts by volume of Water andB parts by weight ofconin its free form the probable formula I produced centratedhydrochloric acid and diazotized by gradual additionoi 0.7 partsby'weight of sodium nitrite. Now the reaction mixture is brought to 1000parts by volume by the addition of water and neutralized by means ofsodium carbonate. Cotton preliminary treated. with an alkaline solutionof 2.3-hydroxynaphthoic-acid-a-naphthyl amid is 5111- mersed into thisdiazo solution whereby the addition of sodium carbonate may be ofadvantage.

The cotton is black shade of good fastness properties, which propertiesare improved by aftertreatment with suitable metal salts. y p

The .dyestufl thus produced onthe fiber has coat (in.

Its solution in stro-ngsulfuric acid isblue.

wampZ"Q.3,2 parts by weight of the dyestufi obtainable by coupling2-hydroxy 4-nitro-l-diazo-benzene withamino-hydroquino'ne-d1m'ethylether are diazotlzed and further treated asdescribed 111 Example 1.:

by this process dyed a deep.

chromium-salts. The blue-black dyeings thus obtainable are'especiallyfast to light. The

' dyestuff, thus produced on the fiber has in its free form the probableformula:

- (i033 (5H Its solution instrong sulfuric acid is violetblue. 0

I claim: 1. New dyestuffs of the probable general formula:

s on N=N comm wherein a: stands for hydrogen or the nitrogroup and 3 fora naphthalene nucleus, said dyestutfs being dark powders, insoluble inwater, sparinglysoluble in the usual organic solvents, soluble in strongsulfuric acid with violet-blue to blue colorations, dyeing cottonblue-black to black shades.

2. The dyestuff of the probable formula:

OCH;

0,N on N==N -CONH CH3 H being a dark powder, difiicultly soluble in theusual organic solvents, soluble in strong sulfuric acid with a violetblue coloration and dyeing cotton blue-black shades.

3. The dyest-ufi of the probable formula:

OCH;

0 011 =N coma 0 CH1 H being a dark powder, diflicultly soluble in theusual organic solvents and dyeing cotton deep black shades.

In testimony whereof I have, hereunto set 4 my hand.

' JO'SEF HALLER.

